diff --git a/test/TestFilePathEvaluation.py b/test/TestFilePathEvaluation.py
new file mode 100644
index 0000000000..68096fef65
--- /dev/null
+++ b/test/TestFilePathEvaluation.py
@@ -0,0 +1,120 @@
+"""Testing file path evaluation when using import_tasks / include_tasks."""
+import textwrap
+
+import pytest
+
+from ansiblelint.runner import Runner
+
+LAYOUT_IMPORTS = {
+    'main.yml': textwrap.dedent(
+        """\
+        ---
+        - hosts: target
+          gather_facts: false
+          tasks:
+            - name: from main import task 1
+              import_tasks: tasks/task_1.yml
+        """
+    ),
+    'tasks/task_1.yml': textwrap.dedent(
+        """\
+        ---
+        - name: from task 1 import task 2
+          import_tasks: tasks/task_2.yml
+        """
+    ),
+    'tasks/task_2.yml': textwrap.dedent(
+        """\
+        ---
+        - name: from task 2 import subtask 1
+          import_tasks: tasks/subtasks/subtask_1.yml
+        """
+    ),
+    'tasks/subtasks/subtask_1.yml': textwrap.dedent(
+        """\
+        ---
+        - name: from subtask 1 import subtask 2
+          import_tasks: tasks/subtasks/subtask_2.yml
+        """
+    ),
+    'tasks/subtasks/subtask_2.yml': textwrap.dedent(
+        """\
+        ---
+        - name: from subtask 2 do something
+          debug:
+            msg: |
+              Something...
+        """
+    ),
+}
+
+LAYOUT_INCLUDES = {
+    'main.yml': textwrap.dedent(
+        """\
+        ---
+        - hosts: target
+          gather_facts: false
+          tasks:
+            - name: from main import task 1
+              include_tasks: tasks/task_1.yml
+        """
+    ),
+    'tasks/task_1.yml': textwrap.dedent(
+        """\
+        ---
+        - name: from task 1 import task 2
+          include_tasks: tasks/task_2.yml
+        """
+    ),
+    'tasks/task_2.yml': textwrap.dedent(
+        """\
+        ---
+        - name: from task 2 import subtask 1
+          include_tasks: tasks/subtasks/subtask_1.yml
+        """
+    ),
+    'tasks/subtasks/subtask_1.yml': textwrap.dedent(
+        """\
+        ---
+        - name: from subtask 1 import subtask 2
+          include_tasks: tasks/subtasks/subtask_2.yml
+        """
+    ),
+    'tasks/subtasks/subtask_2.yml': textwrap.dedent(
+        """\
+        ---
+        - name: from subtask 2 do something
+          debug:
+            msg: |
+              Something...
+        """
+    ),
+}
+
+
+@pytest.mark.parametrize(
+    'ansible_project_layout',
+    (
+        pytest.param(LAYOUT_IMPORTS, id='using only import_tasks'),
+        pytest.param(LAYOUT_INCLUDES, id='using only include_tasks'),
+    ),
+)
+@pytest.mark.xfail(
+    reason='https://github.com/ansible-community/ansible-lint/issues/1446'
+)
+def test_file_path_evaluation(
+    tmp_path, default_rules_collection, ansible_project_layout
+):
+    """Test file path evaluation when using import_tasks / include_tasks in the project.
+
+    Usage of import_tasks / include_tasks may introduce false positive load-failure due
+    to incorrect file path evaluation.
+    """
+    for file_path, file_content in ansible_project_layout.items():
+        full_path = tmp_path / file_path
+        full_path.parent.mkdir(parents=True, exist_ok=True)
+        full_path.write_text(file_content)
+
+    result = Runner(str(tmp_path), rules=default_rules_collection).run()
+
+    assert not result